EP0772579B1 - Benzoylderivate und ihre herstellung - Google Patents

Benzoylderivate und ihre herstellung Download PDF

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Publication number
EP0772579B1
EP0772579B1 EP95926689A EP95926689A EP0772579B1 EP 0772579 B1 EP0772579 B1 EP 0772579B1 EP 95926689 A EP95926689 A EP 95926689A EP 95926689 A EP95926689 A EP 95926689A EP 0772579 B1 EP0772579 B1 EP 0772579B1
Authority
EP
European Patent Office
Prior art keywords
formula
methyl
alkyl
fluoro
compound according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Revoked
Application number
EP95926689A
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English (en)
French (fr)
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EP0772579A1 (de
Inventor
Bruce Cameron Hamper
Kindrick Lee Leschinsky
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Co
Original Assignee
Monsanto Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by Monsanto Co filed Critical Monsanto Co
Publication of EP0772579A1 publication Critical patent/EP0772579A1/de
Application granted granted Critical
Publication of EP0772579B1 publication Critical patent/EP0772579B1/de
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Claims (11)

  1. Verbindung der Formel (I)
    Figure 00150001
    worin
    X1 Fluor bedeutet;
    X2 Chlor darstellt;
    R1 Methyl ist; und
    R2 die Bedeutung H, C1-C6-Alkyl oder C1-C6-Halogenalkyl oder -CH2COR3 hat, wobei R3 C1-C6-Halogenalkyl darstellt.
  2. Verbindung nach Anspruch 1, worin R2 Methyl ist.
  3. Verbindung nach Anspruch 2, worin R3 die Bedeutung -CF3 hat.
  4. Verfahren zur Herstellung von Verbindungen der Formel (IC)
    Figure 00150002
    welches umfaßt: Acylieren einer Verbindung der Formel (IB)
    Figure 00160001
    worin
    X1 und X2 die Bedeutung H oder Halogen haben;
    R1 C1-C6-Alkyl darstellt; und
    R3 C1-C6-Halogenalkyl ist;
    mit einem Ester, Acetylhalogenid oder Anhydrid in einem inerten Lösungsmittel in Anwesenheit einer starken Base, und nach Aufarbeiten Gewinnen der Verbindung der Formel (IC).
  5. Verfahren nach Anspruch 4, wobei X1 Fluor bedeutet; X2 Chlor darstellt; R1 Methyl ist; und R3 die Bedeutung -CF3 hat.
  6. Verfahren nach Anspruch 4, bei welchem die Verbindungen der Formel (IB) hergestellt werden durch das Umsetzen einer Verbindung der Formel (II)
    Figure 00160002
    worin X1, X2 und R1 wie vorstehend definiert sind, mit einem Organometall-Reagenz, gefolgt vom Umsetzen mit einem Oxidationsmittel in einem inerten Lösungsmittel.
  7. Verfahren nach Anspruch 6, bei welchem das Organometall-Reagenz ein Alkyllithium- oder Alkyl-Grignard-Reagenz ist, und das Oxidationsmittel Jones-Reagenz ist.
  8. Verfahren nach Anspruch 7, bei welchem das Organometall-Reagenz Methyllithium oder Methyl-Grignard ist.
  9. Verfahren zur Herstellung von Verbindungen der Formel (IA)
    Figure 00170001
    welches umfaßt: Umsetzen einer Verbindung der Formel (II)
    Figure 00170002
    worin X1, X2 und R1 wie vorstehend definiert sind, mit einem Alkylierungsmittel in Anwesenheit eines Alkylierungskatalysators.
  10. Verfahren nach Anspruch 9, bei welchem das Alkylierungsmittel ein Halogen-C1-C4-alkyl-C1-C4-alkylether ist, und der Katalysator eine Lewis- oder Brønsted-Säure ist.
  11. Verfahren nach Anspruch 9, wobei X1 Fluor bedeutet, X2 Chlor darstellt, R1 Methyl ist, das Alkylierungsmittel Dichlormethylether ist, und der Katalysator ein Metallhalogenid ist.
EP95926689A 1994-07-20 1995-07-14 Benzoylderivate und ihre herstellung Revoked EP0772579B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US27772494A 1994-07-20 1994-07-20
US277724 1994-07-20
PCT/US1995/008839 WO1996002485A1 (en) 1994-07-20 1995-07-14 Benzoyl derivatives and synthesis thereof

Publications (2)

Publication Number Publication Date
EP0772579A1 EP0772579A1 (de) 1997-05-14
EP0772579B1 true EP0772579B1 (de) 1999-03-10

Family

ID=23062100

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95926689A Revoked EP0772579B1 (de) 1994-07-20 1995-07-14 Benzoylderivate und ihre herstellung

Country Status (15)

Country Link
EP (1) EP0772579B1 (de)
JP (1) JPH10503186A (de)
AT (1) ATE177418T1 (de)
AU (1) AU694253B2 (de)
BR (1) BR9508302A (de)
CA (1) CA2193677A1 (de)
CZ (1) CZ11697A3 (de)
DE (1) DE69508251T2 (de)
DK (1) DK0772579T3 (de)
ES (1) ES2129839T3 (de)
GR (1) GR3030190T3 (de)
HU (1) HU215203B (de)
MX (1) MX9700500A (de)
PL (1) PL179920B1 (de)
WO (1) WO1996002485A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5925795A (en) * 1996-09-16 1999-07-20 Zeneca Limited Processes for the preparation of aryl-β-diketones, arylpyrimidine ketones and crop protection intermediates
DE10140148B4 (de) 2001-08-16 2012-07-19 Merck Patent Gmbh Fluorierte Polycyclen und ihre Verwendung in Flüssigkristallmischungen und in Flüssigkristalldisplays
JP6399814B2 (ja) * 2014-06-09 2018-10-03 イハラニッケイ化学工業株式会社 ジクロロメチルアルキルエーテル化合物の製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3268459B2 (ja) * 1991-05-31 2002-03-25 日本農薬株式会社 アセトフェノン類の製造法
JPH06340643A (ja) * 1993-04-04 1994-12-13 Nippon Nohyaku Co Ltd オキサゾ−ル又はチアゾ−ル誘導体及びその製造方法並びに除草剤

Also Published As

Publication number Publication date
DE69508251D1 (de) 1999-04-15
GR3030190T3 (en) 1999-08-31
JPH10503186A (ja) 1998-03-24
PL318351A1 (en) 1997-06-09
CA2193677A1 (en) 1996-02-01
HUT76859A (en) 1997-12-29
DE69508251T2 (de) 1999-10-14
MX9700500A (es) 1997-04-30
BR9508302A (pt) 1997-10-21
AU3098295A (en) 1996-02-16
PL179920B1 (pl) 2000-11-30
HU215203B (hu) 1998-10-28
DK0772579T3 (da) 1999-09-27
EP0772579A1 (de) 1997-05-14
CZ11697A3 (en) 1997-07-16
ES2129839T3 (es) 1999-06-16
WO1996002485A1 (en) 1996-02-01
ATE177418T1 (de) 1999-03-15
AU694253B2 (en) 1998-07-16

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